Deals on vacations and trips to Winchester

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Valley River Inn

Valley River Inn

3.5 out of 5
Price was $1,616, price is now $1,238 per person
$1,238
per person
May 31 - Jun 7
found 3 hours ago
Roundtrip flight included
Springfield (SPI) to Eugene (EUG)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the children's pool and picnic area. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Hayward Inn

Hayward Inn

3 out of 5
East University
Price was $1,971, price is now $1,691 per person
$1,691
per person
May 31 - Jun 7
found 3 hours ago
Roundtrip flight included
Springfield (SPI) to Eugene (EUG)
This hotel features an indoor pool and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Counting Z's

Counting Z's

2 out of 5
Save 100% on your flight
Price was $10,655, price is now $9,337 per person
$9,337
per person
May 31 - Jun 7
found 3 hours ago
Roundtrip flight included
Springfield (SPI) to Eugene (EUG)
This inn features free WiFi in public areas, laundry facilities, and a virtual front desk.
The 505 Eugene

The 505 Eugene

3 out of 5
Downtown Eugene
Price was $1,556, price is now $1,386 per person
$1,386
per person
May 31 - Jun 7
found 3 hours ago
Roundtrip flight included
Springfield (SPI) to Eugene (EUG)
This apartment features a virtual front desk. Take advantage of the free self parking.
The Local Motel & Shops

The Local Motel & Shops

2 out of 5
Downtown Eugene
Price was $1,472, price is now $1,319 per person
$1,319
per person
May 31 - Jun 7
found 3 hours ago
Roundtrip flight included
Springfield (SPI) to Eugene (EUG)

Top Winchester hotels deals

Singing Waters at N. Umpqua

Singing Waters at N. Umpqua

Roseburg North OR
Get rates
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
The Lodge at Roseburg

The Lodge at Roseburg

2.5 out of 5
375 Harvard Blvd Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $147 total per night
$147 total
Mar 19 - Mar 20
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $107 total per night
$107 total
Mar 17 - Mar 18
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's an outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

2.5 out of 5
2855 NW Edenbower Blvd Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $83 total per night
$83 total
Mar 17 - Mar 18
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

2.5 out of 5
3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$66 nightly
The price is $73 total per night
$73 total
Apr 12 - Apr 13
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.
Quality Inn Central Roseburg

Quality Inn Central Roseburg

2.5 out of 5
427 Nw Garden Valley Blvd Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $83 total per night
$83 total
Apr 14 - Apr 15
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. The front desk is staffed around-the-clock and free newspapers are on offer.
Don't see what you're looking for?
See all available properties in Winchester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Winchester?
Starting from as low as $1,238, hotel and flight packages are an excellent way to stretch your travel budget. Winchester, here you come!
Where can I get the best vacation package deals for Winchester?
Snapping up the perfect package deal to Winchester is a piece of cake with Travelocity. With as many as 400 airlines and 1,000,000 properties all over the globe, you're spoiled for choice when selecting your flights and hotels.
Why should I book my Winchester vacation bundle via Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.
Can I save money on my Winchester car rental if I bundle it with hotels and flights?
You sure can with our Winchester vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Bundle any two or more car, hotel, flight and tour bookings and see the savings pile up. With a rental car, all the key sights in and around Winchester are just a road trip away.
Which airport is best for Winchester?
Southwest Oregon Regional Airport (OTH), the primary terminal in Winchester, is where you'll stroll through arrivals. You'll find it 45 mi west of the center of town.
Where should I stay when visiting Winchester?
Many travelers hit the hay at the Singing Waters at N. Umpqua. It's a great base for your Winchester getaway.

Photos of local treasures

Browse Winchester vacation photos for more inspiration